2001年7月
Synthesis of 5-deoxy-5-phosphinyl-D-galactopyranose derivatives: New phospha-sugar analogs of D-galactose
HETEROCYCLES
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- 巻
- 55
- 号
- 7
- 開始ページ
- 1301
- 終了ページ
- 1309
- 記述言語
- 英語
- 掲載種別
- 研究論文(学術雑誌)
- 出版者・発行元
- PERGAMON-ELSEVIER SCIENCE LTD
The addition reaction of dimethyl phosphonate to 3,6-di-O-benzyl-1,2-O-isopropylidene-alpha -L-arabino-hexofuranos-5-ulose (11), followed by deoxygenation of 5-hydroxyl group, provided 5-deoxy-5-dimethoxyphosphinyl-D-galactofuranose derivative (13a). Reduction of 13a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrochloric acid and then hydrogen peroxide, afforded the first D-galactopyranose analog (15) having a phosphinyl group in the hemiacetal ring. This was converted into the 1,2,4-tri-O-acetyl-5-methoxyphosphinyl derivatives (16), whose structure and conformation were established by H-1-NMR spectroscopy.
- リンク情報
- ID情報
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- ISSN : 0385-5414
- Web of Science ID : WOS:000170864800010